Avenaciolide
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| Category | Antibiotics |
| Catalog number | BBF-00612 |
| CAS | 20223-76-1 |
| Molecular Weight | 266.33 |
| Molecular Formula | C15H22O4 |
| Purity | >95% by HPLC |
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Description
It is produced by the strain of Aspergillus avenaceus. A bicyclic bis-butyrolactone; isolated from aspergillus avenaceu; an antifungal agent; inhibits glutamate transport; an atypical ionophore.
Specification
| Related CAS | 16993-42-3 |
| Synonyms | Avenaciolid; Furo(3,4-b)furan-2,6(3H,4H)-dione, dihydro-3-methylene-4-octyl- (VAN) (8CI) |
| Storage | -20°C |
| IUPAC Name | (3aR,4R,6aR)-3-methylidene-4-octyl-4,6a-dihydro-3aH-furo[3,4-b]furan-2,6-dione |
| Canonical SMILES | CCCCCCCCC1C2C(C(=O)O1)OC(=O)C2=C |
| InChI | InChI=1S/C15H22O4/c1-3-4-5-6-7-8-9-11-12-10(2)14(16)19-13(12)15(17)18-11/h11-13H,2-9H2,1H3/t11-,12-,13-/m1/s1 |
| InChI Key | GSTQYRQXFPSWSH-JHJVBQTASA-N |
| Source | Aspergillus sp. |
Properties
| Appearance | Long Flake Crystalline |
| Antibiotic Activity Spectrum | fungi |
| Melting Point | 54-56 °C |
| Solubility | Soluble in ethanol, methanol, DMF or DMSO. Poor water solubility. |
Reference Reading
1. Isolation of (-)-avenaciolide as the antifungal and antimycobacterial constituent of a Seimatosporium sp. Endophyte from the medicinal plant Hypericum perforatum
Mark McLaughlin, Trevor N Clark, John A Johnson, Christopher A Gray, Amanda I Bishop, Larry A Calhoun Nat Prod Commun . 2014 Oct;9(10):1495-6.
An extract of Seimatosporium sp., an endophyte from the Canadian medicinal plant Hypericum perforatum, exhibited significant antifungal and antimycobacterial activity against Candida albicans and Mycobacterium tuberculosis H37Ra. Bioassay guided fractionation led to the isolation of (-)-avenaciolide as the only bioactive constituent of the extract. This is the first report of both the antimycobacterial activity of avenaciolide and its isolation from a Seimatosporium sp. fungus.
2. Synthesis, characterization, absolute structural determination and antifungal activity of a new chlorinated aromatic avenaciolide analogue
Carlito Lariucci, Pedro A Castelo-Branco, Mayura M M Rubinger, Laércio Zambolim, Silvana Guilardi, Leandro de C Alves, Dorila Piló-Veloso, Adeliane R dos Santos, Vanessa M Leite, Ivo Vencato Pest Manag Sci . 2009 Jan;65(1):34-40. doi: 10.1002/ps.1640.
Background:Avenaciolide, a natural product isolated from Aspergillus avenaceus H. Smith, possesses several interesting biological properties, such as antifungal and antibacterial activities and inhibition of glutamate transport in mitochondria. In a study aiming to discover new compounds with antifungal activity, a bis-gamma-lactone analogous to avenaciolide was prepared and characterized by elemental analysis, mass spectrometry, and infrared and NMR spectroscopy.Results:The absolute structures of this compound and of the synthetic precursor (also a bis-gamma-lactone) were determined by X-ray diffraction analysis. The bis-gamma-lactones synthesized crystallize in the orthorhombic space group P2(1)2(1)2(1), and the crystal packings are supported by C--H...O hydrogen bonds. The compound showed antifungal activity against Colletotrichum gloeosporioides (Penz.) Penz. & Sacc., while the synthetic precursor was inactive under the in vitro test conditions employed.Conclusion:The results indicate that it is not only the bis-gamma-lactone skeleton that is important to antifungal activity. The latter also depends on the presence of the exocyclic double bond possibly due to a Michael addition type reaction with the fungal enzymes.
3. Avenaciolide Induces Apoptosis in Human Malignant Meningioma Cells through the Production of Reactive Oxygen Species
Shinji Kamisuki, Takumi Katsuzawa, Yo Shinoda, Kohei Kujirai Biol Pharm Bull . 2022;45(4):517-521. doi: 10.1248/bpb.b21-01039.
Malignant meningioma has a poor prognosis and there are currently no effective therapies. Avenaciolide is water-insoluble natural organic product produced by Aspergillus avenaceus G. Smith that can inhibit mitochondrial function. In the present study, we investigated the anti-cancer effects of avenaciolide in an isolated human malignant meningioma cell line, HKBMM. In addition, to assess the specificity of avenaciolide, its effects on normal human neonatal dermal fibroblast HDFn cells were also examined. Avenaciolide showed effective anti-cancer activity, and its cytotoxicity in HKBMM cells was greater than that in HDFn cells. The anti-cancer effects of avenaciolide were mediated by reactive oxygen species (ROS)-induced apoptosis, which may have been caused by mitochondrial disfunction. These results suggest that avenaciolide has potential as a therapeutic drug for malignant meningioma.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
